Ammonium compounds

ABSTRACT

Ammonium compounds of the formula ##STR1## in which R and R 1  designate C 1  -C 21  -alkyl or C 2  -C 21  -alkenyl, 
     R&#39; designates hydrogen or C 1  -C 4  -alkyl, 
     R 2  designates C 1  -C 4  -alkyl or hydroxy-C 1  -C 4  -alkyl, 
     R 3  designates hydrogen or C 1  -C 4  -alkyl and 
     A.sup.⊖  represents an anion of the formula ##STR2##  in which R 4  designates hydrogen, C 1  -C 4  -alkyl or C 1  -C 4  -alkoxy and 
     R 5  designates C 1  -C 4  -alkyl or C 1  -C 4  -hydroxyalkyl, 
     a process for their preparation and their use as softeners for fibre materials.

The invention relates to new ammonium compounds of the formula ##STR3## in which R and R₁ designate C₁ -C₂₁ -alkyl or C₂ -C₂₁ -alkenyl,

R' designates hydrogen or C₁ -C₄ -alkyl,

R₂ designates C₁ -C₄ -alkyl or hydroxy-C₁ -C₄ -alkyl,

R₃ designates hydrogen or C₁ -C₄ -alkyl and

A.sup.⊖ represents an anion of the formula ##STR4## in which R₄ designates hydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy and

R₅ designates C₁ -C₄ -alkyl or C₁ -C₄ -hydroxyalkyl,

a process for their preparation and their use as softeners for fibre materials.

The following meanings of individual substituents are preferable:

R or R₁ C₁₁ -C₂₁ -alkyl or C₁₁ -C₂₁ -alkenyl; R' hydrogen or methyl; R₃ methyl or ethyl; R₄ hydrogen, methyl, ethyl, methoxy or ethoxy; and R₅ methyl or ethyl.

Those compounds of the formula I are particularly preferable in which R₂ designates methyl and R₃ designates hydrogen, methyl or ethyl.

Preferable anions A.sup.⊖ are: ##STR5##

Ammonium compounds of the formula I are prepared by reacting esters of the formula ##STR6## in which

R, R', R₁ and R₂ have the meanings indicated in the formula I

at temperatures of about 50° to about 200° C., preferably at 100°-150° C., with compounds of the formula ##STR7## in which

R₃, R₄ and R₅ have the meanings indicated in the formulae (I) and (II).

The new compounds are obtained here as solid or pasty products which are readily soluble or dispersible in water.

Preferable compounds are obtained by reacting esters of the formula ##STR8## with trimethyl phosphate, triethyl phosphate, dimethyl methanephosphonate or diethyl ethanephosphonate, but in particular with dimethyl phosphite or diethyl phosphite.

Esters of the formulae III or V can be prepared in a manner which is in itself known, for example by reaction of 2 mols of a corresponding carboxylic acid or of its low alkyl ester with 1 mol of a compound of the formula ##STR9## in which

R' and R₂ have the meanings indicated in the formula I

at temperatures of 100° to 180° C., water formed during the reaction or the lower alcohol being continuously removed from the reaction mixture. For the case that R≠R₁ the amine can first be reacted with one mol of a carboxylic acid and the product then reacted with one mol of another carboxylic acid.

Possible examples of carboxylic acids are not only pure acids, such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid or linoleic acid, but also, if appropriate, acid mixtures, such as possibly hydrogenated fatty acid mixtures on which natural fats are based or fractions of such fatty acid mixtures.

The new ammonium compounds are suitable for use as softeners for fibre materials, such as textile fibre materials made of synthetic fibres, for example of polyester, polyacrylonitrile or polyamide fibres, and, in particular, of cotton or regenerated cellulose fibres. They are also suitable for use as softening agents for paper.

The new compounds are applied to fibre materials in a manner which is customary for softeners, for example by the exhaust method from a long liquor. For this purpose, 0.1 g to 10 g of the new compounds per liter of water are dissolved or dispersed. On application by the pad method, amounts of 5-25 g per liter of liquor are advantageously used.

In the examples which follow, parts are parts by weight.

EXAMPLE 1

241 parts of hydrogenated coconut fatty acid and 22 parts of stearic acid are dissolved in 60 parts of toluene, 75 parts of N-methyl-N,N-diethanolamine are added, and the mixture is heated to 130°-140° C., water formed being distilled off azeotropically.

After toluene has been distilled off, 65 parts of dimethyl phosphite are added to the resulting ester, and the mixture is heated for 4-5 hours at 140° C. After cooling down, the mixture is obtained as a viscous liquid which gives a slightly turbid solution in water. The surface tension of an 0.5% strength aqueous solution at 20° C. is 31.4 mN.m⁻¹.

EXAMPLE 2

35 parts of dimethyl methanephosphonate are added to 165 parts of an ester prepared analogously to Example 1 from 1 mol of stearic acid and 1 mol of lauric acid with 1 mol of N-methyl-N,N-diethanolamine, and the mixture is stirred for 6 hours at 140° C. The result is a water-soluble product which, at room temperature, solidifies to give a pasty material. The surface tension of an 0.5% strength aqueous solution at 20° C. is 35.9 mN.m⁻¹.

EXAMPLE 3

0.5% of the product of Example 1 (relative to the weight of the goods) is dissolved 1:10 in water, and the solution is added to an aqueous liquor, the amount of which, in proportion to the weight of the goods, is 1:20.

The textile material used is cotton terry towelling having a weight per square meter of 100 g/m². The treatment temperature is 40° C., and the treatment time is 30 minutes. The material is then squeezed, in a pad mangle, down to a liquor pick-up of 100% and dried 2-3 minutes at 120° C. The result is a pleasant, soft handle.

EXAMPLE 4

15 g of the ammonium compound prepared according to Example 2 are dissolved 1:10 in water at 40° C. The solution is made up to 1 liter with water. Cotton terry towelling having a square meter weight of 180 g/m² is dipped into the liquor and squeezed off, in a pad mangle, down to a liquor pick-up of 90%. The material is then dried for 2-3 minutes at 120° C. The result is terry towelling fabric having a pleasant, soft handle. 

We claim:
 1. Ammonium compounds of the formula ##STR10## in which R and R₁ designate C₁ -C₂₁ -alkyl or C₂ -C₂₁ -alkenyl,R' designates hydrogen or C₁ -C₄ -alkyl, R₂ designates C₁ -C₄ -alkyl or hydroxy-C₁ -C₄ -alkyl, R₃ designates hydrogen or C₁ -C₄ -alkyl and A.sup.⊖ represents an anion of the formula ##STR11## in which R₄ designates hydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy and R₅ designates C₁ -C₄ -alkyl or C₁ -C₄ -hydroxyalkyl.
 2. Compounds according to claim 1, in which, in the formula I,R and R₁ designate C₁₁ -C₂₁ -alkyl or C₁₁ -C₂₁ -alkenyl, R' designates hydrogen or methyl, R₂ designates C₁ -C₄ -alkyl or hydroxy-C₁ -C₄ -alkyl, R₃ designates methyl or ethyl, R₄ designates hydrogen, methyl, ethyl, methoxy, or ethoxy and R₅ designates methyl or ethyl.
 3. Compounds according to claims 1 and 2, in whichR₂ designates methyl and R₃ designates hydrogen, methyl or ethyl.
 4. Compounds according to claims 1 to 3, characterised in that A.sup.⊖ represents a ##STR12##
 5. Ammonium compounds which can be obtained by reacting compounds of the formula ##STR13## with trimethyl phosphate, triethyl phosphate, dimethyl methanephosphonate or diethyl ethanephosphonate, but, in particular, with dimethyl phosphite or diethyl phosphite.
 6. Process for preparing ammonium compounds according to claim 1, characterized in that esters of the formula ##STR14## in which R, R', R₁ and R₂ have the meanings indicated in claim 1at temperatures of about 50° to about 200° C. with compounds of the formula ##STR15## in which R₃, R₄ and R₅ have the meanings indicated in claim
 1. 7. Use of compounds according to claims 1 to 5, as softeners for fibre materials. 